Hydrochloric Acid → HCID 67197005, compound

HRID 1423074Notes

Reaction equation

HRID 1423074 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH:11]=[C:12]([C:14]#[N:15])[CH:13]=1)=[O:4].[OH-].[Na+].Cl>CO.O>[C:14]([C:12]1[CH:13]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2[CH:7]=[CH:8][N:9]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:10]=2[CH:11]=1)#[N:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67198451HCID 67198451, compound

Product 1

HCID 67197005HCID 67197005, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred solution of 6-cyano-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid methyl ester (0.34 g, 1.2 mmol) in a mixture of MeOH—H2O (20 mL:5 mL) is added 2 N aqueous NaOH (40 mL) and the mixture is warmed at reflux. After 1 hour, the reaction is cooled to room temperature. The solution is acidified with 2 N aqueous HCl (pH=3). The solid is collected by filtration, washed with CH2Cl2 and dried to afford the title compound.

Workup

  1. temperaturethe mixture is warmed
  2. temperatureat reflux
  3. filtrationThe solid is collected by filtration
  4. washwashed with CH2Cl2
  5. customdried

Sources & evidence

ORD record
ord-71db731509a84a9fb1776eaad77141fe
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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